Hydrochloric Acid → HCID 20588789, compound

HRID 565161Notes

Reaction equation

HRID 565161 reaction equation
[CH:1]([CH:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]#[C:17][C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)=[CH:2][CH3:3].C1(S([O-])=O)C=CC=CC=1.[Na+].Cl.C1(C)C=CC=CC=1>C1COCC1>[CH:1](/[CH:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:11]=[CH:12][C:13]([C:16]#[C:17][C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)=[CH:14][CH:15]=2)[CH2:6][CH2:5]1)=[CH:2]\[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 2723840Benzenesulfinic acid, sodium saltHCID 73689151HCID 73689151, compound

Product 1

HCID 20588789HCID 20588789, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

26.0 g of 1-propenyl-4-(4-p-tolylethynylphenyl)cyclohexane from Example 9, 10.34 g of sodium benzenesulphinate, 100 ml of 2 N hydrochloric acid solution, 175 ml of toluene and 87 ml of THF were combined and heated to reflux. After 4 hours, the reaction mixture was allowed to cool, and the aqueous phase was removed. A further 10.34 g of sodium benzenesulphinate and 100 ml of 2 N hydrochloric acid solution were then added, and the mixture was refluxed for a further 2 hours, the aqueous phase was again removed after cooling, and a further 10.34 g of sodium benzenesulphinate and 100 ml of 2 N hydrochloric acid solution were added, the mixture was refluxed overnight, and subsequently subjected to conventional work-up, giving 1-E-propenyl-4-(4-p-tolylethynylphenyl)cyclohexane in the form of a colourless solid.

Workup

  1. temperatureheated to reflux
  2. temperatureto cool
  3. customthe aqueous phase was removed
  4. additionA further 10.34 g of sodium benzenesulphinate and 100 ml of 2 N hydrochloric acid solution were then added
  5. temperaturethe mixture was refluxed for a further 2 hours
  6. customthe aqueous phase was again removed
  7. temperatureafter cooling
  8. additiona further 10.34 g of sodium benzenesulphinate and 100 ml of 2 N hydrochloric acid solution were added
  9. temperaturethe mixture was refluxed overnight

Sources & evidence

ORD record
ord-7fc76a6944774ec2b99b1ef35aa485e5
Source dataset
uspto-grants-2001_01
Patent number
US06171664B2

Reaction notes

Loading…